An operating system conversion (OSC) computing device generates a custom archive file including an OS image file associated with a second operating system (OS) for a host computing device having a first OS. The OSC computing device formats a data storage device of the host computing device to include a first partition associated with the first OS and a second partition associated with the second OS, transmits the custom archive file to the host computing device, and generates, using the custom archive file, a loopback file system mounted to the host computing device to emulate a physical data storage device. The OS image file is accessible though the loopback file system. The OSC computing device stores the OS image file within an install directory of the second partition and converts an OS operating on the host computing device from the first OS to the second OS.